Asymmetric Redox Allylic Alkylation to Access 3,3′‐Disubstituted Oxindoles Enabled by Ni/NHC Cooperative Catalysis
Tao Fan, Jin Song, Liu‐Zhu Gong
Abstract
The feasibility of cooperative catalysis between chiral N-heterocyclic carbenes and nickel in asymmetric reactions has been demonstrated convincingly. The high efficiency of this catalytic system enables the asymmetric allylic alkylation of isatin-derived enals with allylic carbonates and [3+3] annulation with racemic vinyl epoxides to provide straightforward access to highly enantioenriched 3,3'-disubstituted oxindoles. The great practicality of this method in organic synthesis has been showcased by facile product modification and enantioselective synthesis of the key building block to access (-)-debromoflustramine B.
Topics & Concepts
Enantioselective synthesisAllylic rearrangementCatalysisTsuji–Trost reactionCombinatorial chemistryAlkylationAnnulationChemistryIsatinOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods